33253-32-6

Upstream product

• 3155-51-9 7,8-dihydro-4-methoxy-6-styryl-2H-pyran-2-one 
• 675-10-5 4-hydroxy-6-methyl-2-pyron 
• 100-44-7 benzyl chloride 
• 2021-28-5 ethyl dihydrocinnamate 
• 100-39-0 benzyl bromide 

Downstream Products

• 162174-71-2 6-(α-ethyl-phenethyl)-4-hydroxy-2H-pyran-2-one 
• 158200-29-4 3-(α-ethylbenzyl)-6-phenethyl-4-hydroxy-2H-pyran-2-one 
• 1259313-10-4 4-bromo-6-phenethyl-2-pyrone 
• 1259312-82-7 4-(2-iodophenoxy)-6-phenethyl-2-pyrone 
• 1259312-69-0 9-phenethylbenzofuro[3,2-c]-2-pyrone 
• 1642145-09-2 4-{1-[(tert-butyldimethylsilanyloxy)methyl]propoxy}-6-(2-phenylethyl)-2-pyrone 
• 162169-82-6 3-(α-cyclopropyl-meta-(4-cyanophenylsulfonylamino)benzyl)-6-(α-ethylphenethyl)-4-hydroxy-2H-pyran-2-one 

Relevant academic research and scientific papers

HIV-1 integrase and neuraminidase inhibitors from alpinia zerumbet

AIDS and influenza are viral pandemics and remain one of the leading causes of human deaths worldwide. The increasing resistance of these diseases to synthetic drugs demands the search for novel compounds from plant-based sources. In this regard, the leav

Syntheses of 2-pyrones via electrophilic substitutions at C7 of 4-hydroxy-6-methyl-2-pyrone through mono- or dianion formation

Electrophilic substitution protocols useful for functionalizations at C7 of 4-hydroxy-6-methyl-2-pyrone, or triacetic acid, are described here. This method was applied to the synthesis of annularin E. Georg Thieme Verlag Stuttgart.

Syntheses and biological activities of dihydro-5,6-dehydrokawain derivatives

The syntheses and biological activities of dihydro-5,6-dehydrokawain derivatives against plant pathogenic fungi and termites were investigated. Dihydro-5,6-dehydrokawain was isolated by a simple method withont chromatography from the leaves of Alpinia spe

Biomimetic iterative method for polyketide synthesis

An iterative method for synthesizing polyketides was demonstrated, in which the chain elongation of a carboxylic acid was performed by decarboxylative dehydration condensation with a malonic acid half thioester. After transforming the resulting β-ketothioester into an appropriate form, the carboxylic acid functionality was regenerated for the next elongation step.

4-hydroxy-6-alkyl-2-pyrones as nucleophilic coupling partners in Mitsunobu reactions and oxa-Michael additions

Two mild and efficient strategies have been developed for the O-functionalisation of 4-hydroxy-6-alkyl-2-pyrones, by using them as nucleophilic partners in oxa-Michael additions and the Mitsunobu reaction. The reactions proceed in moderate to excellent yields on a range of substrates containing useful functionality. The reactions serve as practical and valuable synthetic methods to construct complex 2-pyronyl ethers, which are found embedded in a number of natural products.

Pyran-2-ones and 5,6-dihydropyran-2-ones useful for treating hyperplasia and other diseases

Certain 2H-pyran-2-ones are useful for treating benign prostatic hypertrophy or hyperplasia, prostatic cancer, alopecia, hirsutism, acne vulgaris and seborrhea.

Syntheses and biological activities of pyranyl-substituted cinnamates

Twenty-two kinds of pyranyl-substituted cinnamates were synthesized by the reaction of 4-hydroxy-6-(2-phenylethyl)-2H-pyran-2-one or 4-hydroxy-6-methyl-2H-pyran-2-one (HMP) with a variety of substituted cinnamic acids, and their antifungal and plant growth inhibitory activities were investigated. Among the compounds prepared, 6-methyl-2-oxo-2H-pyran-4-yl 3-(4-isopropylphenyl)propenoate (H5) showed the strongest antifungal activity against Rhizoctonia solani and Sclerotium dellfinii, and 6-methyl-2-oxo-2H-pyran-4-yl 3-(2-methylphenyl)propenoate (H2) had the highest plant growth inhibitory activity toward Brassica rapa.

PYRANONE COMPOUNDS USEFUL TO TREAT RETROVIRAL INFECTIONS

The present invention relates to compounds of formulae (I) and (II) which are pyran-2-ones, 5,6-dihydro-pyran-2-ones, 4-hydroxy-benzopyran-2-ones, 4-hydroxy-cycloalkyl[b]pyran-2-ones, and derivatives thereof, useful for inhibiting a retrovirus in a mammalian cell infected with said retrovirus, wherein R 10 and R 20 taken together are formulae (III) and (IV). STR1

Structure-Based Design of Novel HIV Protease Inhibitors: Carboxamide-Containing 4-Hydroxycoumarins and 4-Hydroxy-2-pyrones as Potent Nonpeptidic Inhibitors

The low oral bioavailability and rapid biliary excretion of peptide-derived HIV protease inhibitors have limited their utility as potential therapeutic agents.Our broad screening program to discover nonpeptidic HIV protease inhibitors had previously identified compound II (phenprocoumon, Ki = 1 μM) as a lead template.Crystal structures of HIV protease complexes containing the peptide-derived inhibitor I (1-(naphthoxyacetyl)-L-histidyl-5(S)-amino-6-cyclohexyl-3(R),4(R)-dihydroxy-2(R)-isopropylhexanoyl-L-isoleucine N-(2-pyridylmethyl)amide) and nonpeptidic inhibitors, such as phenprocoumon (compound II), provided a rational basis for the structure-based design of more active analogues.This investigation reports on the important finding of a carboxamide functionality appropriately added to the 4-hydroxycoumarin and the 4-hydroxy-2-pyrone templates which resulted in new promising series of nonpeptidic HIV protease inhibitors with improved enzyme-binding affinity.The most active diastereomer of the carboxamide-containing compound XXIV inhibited HIV-1 protease with a Ki value of 0.0014 μM.This research provides a new design direction for the discovery of more potent HIV protease inhibitors as potential therapeutic agents for the treatment of HIV infection.